Gautam Gupta had it all. He was just 26 and a rising venture capitalist with a bright future and a big salary. An associate at General Catalyst Partners, he’d sourced six deals, deployed $65 million and had just opened General Catalyst’s Palo Alto office.

Then he threw it all away to launch a startup. And not some cool startup with a mobile-social app poised to be acquired for $1 billion. An e-commerce startup. Even his mother began to wonder.